Compound for organic electric element, organic electric element using the same, and electronic device thereof

ABSTRACT

Provided are a compound capable of improving luminous efficiency, stability and lifetime of an organic electronic device, an organic electric element using the same, and an electronic device comprising the element.

BACKGROUND Technical Field

The present invention relates to compound for organic electric element, organic electric element using the same, and an electronic device thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenon that converts electric energy into light energy by using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is often composed of a multi-layered structure composed of different materials, and for example, may include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electric element may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like depending on its function.

And the light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and into a fluorescent material derived from the singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons depending on the light emitting mechanism. Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color.

Meanwhile, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuation effect, therefore a host/dopant system can be used as a light emitting material in order to increase luminous efficiency through increase of color purity and energy transfer. When the small amount of dopant having a smaller energy band gap than the host forming the emitting layer is mixed on the emitting layer, the excitons generated in the emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of the dopant used.

Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.

Efficiency, life span, driving voltage and the like are related to each other. As the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage drops, the crystallization of the organic material due to joule heating generated during driving is reduced, and as a result, the life span tends to increase. However, simply improving the organic material layer cannot maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time. Therefore, it is necessary to develop a light emitting material having a high thermal stability and achieving a charge balance in the emitting layer efficiently.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electric element, a material for forming an organic material layer in an element such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an emitting-auxiliary layer material, and the like should be supported by stable and efficient materials. However, such a stable and efficient organic material layer material for an organic electric element has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and especially development of host materials for the emitting layer is urgently required.

Otherwise, in the case of a polycyclic compound including a heteroatom, the difference in properties according to the material structure is so large that it is applied to various layers as OLED material. In particular, it has characteristics of different band gaps (HOMO, LUMO), electrical characteristics, chemical properties, and physical properties depending on the number of rings, fused positions and the type and arrangement of heteroatoms, therefore application development for various OLED layers using the same has been progressed. Recently, development of OLED material for heteroatom type, number and position of pentacyclic compounds has been actively developed.

As a precedent reference, U.S. Pat. No. 8,334,058 B2 is referred to.

DETAILED DESCRIPTION OF THE INVENTION Summary

Using the characteristics of the polycyclic compound, the present invention provides a compound capable of maximizing the effect of improving luminous efficiency and long life, while maintaining or slightly reducing the driving voltage of the device, and an organic electric element using the same and an electronic device thereof.

Technical Solution

The present invention provides compounds represented by Formula (1) and Formula (18), organic electric elements comprising the same and electronic devices thereof.

Effects of the Invention

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the element, and can greatly improve the color purity and lifetime of the element.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE illustrates an example of an organic electric element according to the present invention.

  100 organic electric element, 110 substrate 120 the first electrode (anode), 130 the hole injection layer 140 the hole transport layer, 141 a buffer layer 150 the emitting layer, 151 the emitting auxiliary layer 160 the electron transport layer, 170 the electron injection layer 180 the second electrode (cathode)

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be described in detail. Further, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the like may be used herein when describing components of the present invention. Each of these terminologies is not used to define an essence, order or sequence of a corresponding component but used merely to distinguish the corresponding component from other component(s). It should be noted that if a component is described as being “connected”, “coupled”, or “connected” to another component, the component may be directly connected or connected to the other component, but another component may be “connected”, “coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein, includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as used herein, has a single bond of 1 to 60 carbon atoms, and means saturated aliphatic functional radicals including a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl group substituted with a alkyl or an alkyl group substituted with a cycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, as used herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, means alkyl substituted one or more of carbon atoms consisting of an alkyl with heteroatom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as used herein, has double or triple bonds of 2 to 60 carbon atoms, but is not limited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or “alkyloxy group”, as used herein, means an oxygen radical attached to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group” or “alkenyloxy group”, as used herein, means an oxygen radical attached to an alkenyl group, but is not limited thereto, and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”, as used herein, means an oxygen radical attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, as used herein, has 6 to 60 carbon atoms, but is not limited thereto. Herein, the aryl group or arylene group means a monocyclic and polycyclic aromatic group, and may also be formed in conjunction with an adjacent group. Examples of “aryl group” may include a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an aryl group. For example, an arylalkyl may be an alkyl substituted with an aryl, and an arylalenyl may be an alkenyl substituted with aryl, and a radical substituted with an aryl has a number of carbon atoms as defined herein.

Also, when prefixes are named subsequently, it means that substituents are listed in the order described first. For example, an arylalkoxy means an alkoxy substituted with an aryl, an alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl also means an alkenyl substituted with an arylcarbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, means alkyl including one or more of heteroatoms. Unless otherwise stated, the term “heteroaryl group” or “heteroarylene group”, as used herein, means a C2 to C60 aryl including one or more of heteroatoms or arylene group, but is not limited thereto, and includes at least one of monocyclic and polycyclic rings, and may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heterocyclic group”, as used herein, contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any one of monocyclic and polycyclic rings, and may include heteroaliphadic ring and/or heteroaromatic ring. Also, the heterocyclic group may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein, represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂ instead of carbon consisting of cycle. For example, “heterocyclic group” includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term “aliphatic ring”, as used herein, means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, is represented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether”, as used herein, is represented by —R—O—R′, wherein R or R′ may be independently hydrogen, an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, as used herein, means that substitution is substituted by at least one substituent selected from the group consisting of, but is not limited thereto, deuterium, halogen, an amino group, a nitrile group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylamine group, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the present invention, as used herein, is applied in the same manner as the substituent definition according to the definition of the exponent of the following Formula.

Wherein, when a is an integer of zero, it means the substituent R¹ is absent. That is, when a is 0, it means that all the carbons forming the benzene ring are bonded to hydrogen. In this case, the sign of the hydrogen bonded to the carbon may be omitted and the formula or compound may be described. When a is an integer of 1, the sole substituent R¹ is linked to any one of the carbon constituting the benzene ring, when a is an integer of 2 or 3, they are respectively bonded as follows, in which R¹ may be the same as or different from each other, and when a is an integer of 4 to 6, and it is bonded to the carbon of the benzene ring in a similar manner, whereas the indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present invention and an organic electric element comprising the same will be described.

According to a specific example of the present invention, there is provided a compound represented by Formula (1).

{In Formula (1),

1) Ar¹, Ar² and Ar³ are each independently a C₆-C₆₀ aryl group; 2) l+e is an integer of 0 to 4, d+m is an integer of 0 to 4, a and b are an integer of 0 to 3, n is an integer of 1 to 3, c is an integer of 0 to 4, 3) R¹, R², R³, R⁴ and R⁵ are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); wherein, L′ may be selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; and the R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or a plurality of R¹, a plurality of R², a plurality of R³, a plurality of R⁴, and a plurality of R⁵ may be bonded to each other to form an aromatic ring or and heteroaromatic ring,

wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may be bonded to each other to form a ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed by the combination thereof and comprises a saturated or unsaturated ring.}

In a specific aspect of the invention, the compound represented by Formula (1) comprises a compound represented by any of Formulas (2) to (7) below.

<Formula (5)><Formula (6)><Formula (7)>

Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined above.}

Preferably, at least one of Ar¹, Ar², and R³ in Formula (1) comprises a C₆˜C₂₄ aryl group, more preferably, Ar¹ or Ar³ in Formula (1) comprises a C₆˜C₂₄ aryl group.

Also, R³ in Formula (1) is a C₆˜C₂₄ aryl group.

Also, Formula (1) comprises a compound represented by any of the following Formulas (8) to (10)

{In Formulas (8) to (10),

Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined above.}

Also, the compound represented by Formula (1) comprises compounds represented by Formula (11)

{In Formula (11),

Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined above.}

Specifically, in the present invention, the compound represented by Formula (1) includes the following compounds P-1 to P-160.

In another aspect, the present invention provides an organic electric element comprising a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode and including a compound included in Formula (1).

Wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emitting auxiliary layer, an emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one of the hole injection layer, the hole transport layer, the emitting auxiliary layer, the emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer comprises one compound or 2 or more compounds of Formula (1). Preferably, the compound is included in the emitting layer.

More specifically, the present invention provides an organic electronic element further comprising a compound represented by Formula (12) in the emitting layer.

{In Formula (12),

1) Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵ and Z¹⁶ are each independently CR or N, wherein R is hydrogen; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀ arylamine group; a fluorene group; and is possible to form a ring by combining with neighboring groups, 2) L² is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a C₃-C₆₀ heteroarylene group; and a divalent aliphatic hydrocarbon group;

3) W is NAr⁵, O, S or CR′R″;

R′ and R″ are each independently selected from the group of a C₁-C₅₀ alkyl group; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bonded to each other to form a spiro. 4) Ar⁴ and Ar⁵ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀ arylamine group; a fluorene group}

Formula (12) comprises a compound represented by any of the following Formulas (13) to (16).

{In Formulas (13) to (16),

Ar⁴, Ar⁵, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵, Z¹⁶, L², R′, R″ are the same as defined above.}

Preferably, both Ar⁴ and Ar⁵ of Formula (12) comprise a compound represented by a C₆-C₃₀ aryl group.

Also, the compound represented by Formula (12) comprises a compound represented by Formula (17)

{In Formula (17),

Ar⁴, Ar⁵, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵, Z¹⁶, and L² are the same as defined above. 1) L¹ is selected from the group of a single bond; a C₆-C₆₀ arylene group; a C₃-C₆₀ heteroarylene group; and a divalent aliphatic hydrocarbon group;

2) Y is O, S or NAr⁵,

3) R^(a) and R^(b) are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or a plurality of R^(a) and a plurality of R^(b) may be bonded to each other to form an aromatic ring or and heteroaromatic ring, 4) y is an integer of 0 to 3, and z is an integer of 0 to 4}

Specifically, the compound represented by Formula (12) comprises the following compounds 4-1 to 4-52

As another example, the present invention provides an organic electronic element comprising an anode; a cathode; an organic material layer formed between the anode and the cathode; wherein the organic material layer includes an emitting layer, an hole transport layer formed between the anode and the emitting layer; an emitting auxiliary layer formed between the emitting layer and the hole transport layer; wherein the hole transport layer or the emitting auxiliary layer comprises a compound represented by Formula (18), and the emitting layer comprises a compound represented by Formula (1).

{In Formula (1) and Formula (18),

1) Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined above.} 2) Ar⁴ and Ar⁵ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));

wherein, L′ may be selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group;

and the R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or Ar⁴ and Ar⁵ may be bonded to each other to form a ring. 3) Ar⁶ is selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or is at least one of the following Formulas (1-a), (1-b), (1-c)

4) Ar⁹, Ar¹⁰ and Ar¹¹ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); 5) h, i and g are an integer of 0 to 4; j is an integer of 0 to 3; R⁶, R⁷, R⁸ and R⁹ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));

wherein in case g, h, i, j are 2 or more, R⁶, R⁷, R⁸ and R⁹ are each in plural being the same or different, and may be bonded to each other to form a ring,

6) L⁶ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; 7) L⁵ is selected from the group consisting of a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P}

The present invention also provides an organic electronic element including at least one compound represented by Formula (12) in the emitting layer.

Also, the hole transport layer comprises a compound represented by Formula (19) or Formula (20), and the emitting auxiliary layer comprises a compound represented by Formula (21) or Formula (22)

{In Formulas (19) to (22),

1) Ar⁶ is selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; 2) Ar⁴, Ar⁵, Ar⁹, Ar¹⁰, Ar¹¹, h, i, g, L⁵, L⁶, R⁶, R⁷, R⁸ and R⁹ are the same as defined above.}

Specifically, the compound represented by Formula (18) comprises the following compounds 13-1 to 13-79 and compounds 2-1 to 2-76.

As another example, the present invention provides an organic electronic element comprising an anode; a cathode; an organic material layer formed between the anode and the cathode; wherein the organic material layer includes an emitting layer, an hole transport layer formed between the anode and the emitting layer; an emitting auxiliary layer or an electron blocking layer (EBL) formed between the emitting layer and the hole transport layer; wherein the emitting auxiliary layer or the electron blocking layer comprises a compound represented by Formula (30).

{In Formula (30),

R²⁰, R²¹, R²², R²³, R²⁴, and R²⁵ are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₃₀ aryl group; a fluorenyl group; a C₂-C₃₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₃₀ aliphatic ring and a C₆-C₃₀ aromatic ring; a C₁-C₃₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; or a plurality of R²⁰, a plurality of R²², a plurality of R²³, a plurality of R²⁴, and a plurality of R²⁵ may be bonded to each other to form an aromatic ring or and heteroaromatic ring,

v is an integer of 0 to 3,

u, w, x and y are each independently an integer of 0 to 4, Z is an integer of 0 to 5, L²⁰ and L²¹ are each independently a single bond; a C₆-C₃₀ arylene group; a C₃-C₃₀ heteroarylene group;

Ar²⁰ is a C₆-C₃₀ aryl group; or a C₃-C₃₀ heteroarylene group;

X²⁰ is O, S, NR′ or CR′R″

R′ and R″ are each independently selected from the group of a C₁-C₃₀ alkyl group; a C₆-C₃₀ aryl group; a C₃-C₃₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bonded to each other to form a spiro.}

In present invention, the compound represented by Formula (30) is represented by any of the Formulas (31) to (38)

{In Formulas (31) to (40),

R²⁰, R²¹, R²², R²³, R²⁴, R²⁵, L²⁰, L²¹, Ar²⁰ and X²⁰, u, v, w, x, y and z are the same as defined above.}

In the present invention, the compound represented by Formula (30) comprises the following compounds.

Referring to the FIGURE, the organic electric element (100) according to the present invention includes a first electrode (120) formed on a substrate (110), a second electrode (180), and an organic material layer including the compound represented by Formula (1) between the first electrode (120) and the second electrode (180). Here, the first electrode (120) may be an anode (positive electrode), and the second electrode (180) may be a cathode (negative electrode). In the case of an inverted organic electric element, the first electrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer (130), a hole transport layer (140), an emitting layer (150), an emitting auxiliary layer (151), an electron transport layer (160), and an electron injection layer (170) formed in sequence on the first electrode (120). Here, the remaining layers except the emitting layer (150) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, an emitting-auxiliary layer (151), an electron transport auxiliary layer, a buffer layer (141), etc., and the electron transport layer (160) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to the present invention may further include a protective layer formed on at least one side of the first and second electrodes, which is a side opposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electrical characteristics, the interface characteristics, and the like may vary depending on which substituent is bonded at which position, therefore the choice of core and the combination of sub-substituents associated therewith is also very important, and in particular, when the optimal combination of energy levels and T1 values and unique properties of materials (mobility, interfacial characteristics, etc.) of each organic material layer is achieved, a long life span and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form a cathode, and the organic material layer including the hole injection layer (130), the hole transport layer (140), the emitting layer (150), the electron transport layer (160), and the electron injection layer (170) is formed thereon, and then depositing a material usable as a cathode thereon can manufacture an organic electroluminescent device according to an embodiment of the present invention. In addition, an emission auxiliary layer (151) may be further formed between the hole transport layer (140) and the emitting layer (150), and an electron transport auxiliary layer may be further formed between the emitting layer (150) and the electron transport layer (160).

As another specific example, the present invention provides an organic electric element wherein the emitting layer in the organic material layer is a phosphorescent light emitting layer.

The compounds represented by Formula (1) and (18) are mixed in a ratio of any one of 1:9 to 9:1 to be included in the emitting layer of the organic material layer, wherein the compound represented by Formula (12) is further mixed to be included in the emitting layer.

The present invention may further include a light efficiency enhancing layer formed on at least one of the opposite side to the organic material layer among one side of the first electrode, or one of the opposite side to the organic material layer among one side of the second electrode.

As another example, the present invention provides an organic electronic device wherein the compound represented by Formula (30) is used in an emitting auxiliary layer or an electron blocking layer and is preferably included in a green emitting auxiliary layer. More specifically, the compound represented by Formula (39) or Formula (40) is included in the green emitting auxiliary layer.

Also, the present invention provides the organic electric element wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process, and since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

The organic electric element according to an embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and excellent fairness, and can be manufactured using conventional LCD color filter technology. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Representatively, there are side-by-side arrangement of the radiation part of the R (red), G (green) and B (blue), a stacking method in which R, G, and B emitting layers are laminated on top and bottom, electroluminescence by the blue (B) organic emitting layer and, by using the light from this, a color conversion material (CCM) method using a photo-luminescence of an inorganic phosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising a display device including the organic electric element; and a control unit for driving the display device.

According to another aspect, the present invention provides an display device wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor (organic TFT) and an element for monochromic or white illumination. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula (1) and (2) of the present invention and preparation examples of the organic electric element of the present invention will be described in detail by way of example, but are not limited to the following examples.

Synthesis Example 1

Final product 1 represented by Formula (1) according to the present invention is prepared by reacting Core and Sub as shown in Reaction Scheme 1 below, but is not limited thereto.

Synthesis Example of Core

The Core of the Reaction Scheme 1 can be synthesized by the reaction path of the following Reaction Schemes 2, but is not limited thereto.

Synthesis of Inter-1

In a round bottom flask, 2,4,6-trichloro-1,3,5-triazine (50 g, 410.1 mmol), phenylboronic acid (83.2 g, 451.1 mmol), Pd(PPh₃)₄ (14.2 g, 12.3 mmol), K₂CO₃ (170 g, 1.2 mol), THF (1.3 L) and water (700 ml) were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 55 g (yield: 60%) of Inter 1.

Synthesis of Core

In a round bottom flask, Inter-1 (10 g, 47 mmol), dibenzo[b,d]furan-3-ylboronic acid (12 g, 51.9 mmol), Pd(PPh₃)₄ (1.6 g, 1.4 mmol), K₂CO₃ (20 g, 141 mmol), THF (160 ml), and water (80 ml) were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 5.7 g (yield: 53%) of Core 1.

Examples of the Core are as follows, but are not limited thereto. In addition, [Table 1] shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Core.

TABLE 1 Compound FD-MS Core 1 m/z = 357.07 (C₂₁H₁₂ClN₃O = 357.80) Core 2 m/z = 362.10 (C₂₁H₇D₅ClN₃O = 362.83) Core 3 m/z = 407.08 (C₂₅H₁₄ClN₃O = 407.86) Core 4 m/z = 407.08 (C₂₅H₁₄ClN₃O = 407.86) Core 5 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 6 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 7 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 8 m/z = 457.10 (C₂₉H₁₆ClN₃O = 457.92) Core 9 m/z = 509.13 C₃₃H₂₀ClN₃O = 509.99) Core 10 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 11 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 12 m/z = 483.11 (C₃₁H₁₈ClN₃O = 483.96) Core 13 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 14 m/z = 483.11 (C₃₁H₁₈ClN₃O = 483.96) Core 15 m/z = 509.13 (C₃₃H₂₀ClN₃O = 509.99) Core 16 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 17 m/z = 483.11 (C₃₁H₁₈ClN₃O = 483.96) Core 18 m/z = 509.13 (C₃₃H₂₀ClN₃O = 509.99) Core 19 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 20 m/z = 438.13 (C₂₇H₁₁D₅ClN₃O = 438.93)

Example of Sub

Examples of Sub are as follows, but are not limited thereto. In addition, [Table 2] shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub.

TABLE 2 Compound FD-MS Sub 1 m/z = 304.07 (C₁₈H₁₃BO₂S = 304.17) Sub 2 m/z = 304.07 (C₁₈H₁₃BO₂S = 304.17) Sub 3 m/z = 354.09 (C₂₂H₁₅BO₂S = 354.23) Sub 4 m/z = 354.09 (C₂₂H₁₅BO₂S = 354.23) Sub 5 m/z = 354.09 (C₂₂H₁₅BO₂S = 354.23) Sub 6 m/z = 380.10 (C₂₄H₁₇BO₂S = 380.27) Sub 7 m/z = 404.10 (C₂₆H₁₇BO₂S = 404.29) Sub 8 m/z = 380.10 (C₂₄H₁₇BO₂S = 380.27) Sub 9 m/z = 385.14 (C₂₄H₁₂D₅BO₂S = 385.30) Sub 10 m/z = 430.12 (C₂₈H₁₉BO₂S = 430.33) Sub 11 m/z = 430.12 (C₂₈H₁₉BO₂S = 430.33) Sub 12 m/z = 480.14 (C₃₂H₂₁BO₂S = 480.39) Sub 13 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 14 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 15 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 16 m/z = 380.10 (C₂₄H₁₇BO₂S = 380.27) Sub 17 m/z = 385.14 (C₂₄H₁₂D₅BO₂S = 385.30) Sub 18 m/z = 430.12 (C₂₈H₁₉BO₂S = 430.33) Sub 19 m/z = 430.12 (C₂₈H₁₉BO₂S = 430.33) Sub 20 m/z = 480.14 (C₃₂H₂₁BO₂S = 480.39) Sub 21 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 22 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 23 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37)

Synthesis Example of Product Synthesis Example of P-41

In a round bottom flask, Core 2 (5 g, 14 mmol), Sub 1 (4.6 g, 15.2 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.7 g, 41.3 mmol), THF and water were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 4.6 g (yield: 57%) of P-41.

Synthesis Example of P-91

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub 9 (5.8 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THF and water were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 4.7 g (yield: 51%) of P-91.

Synthesis Example of P-106

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub 16 (5.8 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THF and water were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 5.8 g (yield: 63%) of P-106.

Synthesis Example of P-146

In a round bottom flask, Core 11 (5 g, 14 mmol), Sub 2 (5.8 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THF and water were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 4.7 g (yield: 51%) of P-146.

Synthesis Example of P-4

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub 6 (5.9 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THF and water were added and stirred at 90° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 6.1 g (yield: 66%) of P-4. [Table 3] shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Product.

TABLE 3 compound FD-MS P-1 m/z = 581.16 (C₃₉H₂₃N₃OS = 581.69) P-2 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-3 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-4 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-5 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-6 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-7 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-8 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-9 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-10 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-11 m/z = 586.19 (C₃₉H₁₈D₅N₃OS = 586.72) P-12 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-13 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-14 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-15 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-16 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-17 m/z = 636.20 (C₄₃H₂₀D₅N₃OS = 636.78) P-18 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-19 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-20 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-21 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-22 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-23 m/z = 636.20 (C₄₃H₂₀D₅N₃OS = 636.78) P-24 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-25 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-26 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-27 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-28 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-29 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-30 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-31 m/z = 581.16 (C₃₉H₂₃N₃OS = 581.69) P-32 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-33 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-34 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-35 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-36 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-37 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-38 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-39 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-40 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-41 m/z = 586.19 (C₃₉H₁₈D₅N₃OS = 586.72) P-42 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-43 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-44 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-45 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-46 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-47 m/z = 636.20 (C₄₃H₂₀D₅N₃OS = 636.78) P-48 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-49 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-50 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-51 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-52 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-53 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-54 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-55 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-56 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-57 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-58 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-59 m/z = 662.22 (C₄₅H₂₂DN₃OS = 662.82) P-60 m/z = 662.22 (C₄₅H₂₂DN₃OS = 662.82) P-61 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-62 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-63 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-64 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-65 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-66 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-67 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-68 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-69 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-70 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-71 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-72 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-73 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-74 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-75 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-76 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-77 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-78 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-79 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-80 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-81 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-82 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-83 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-84 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-85 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-86 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-87 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-88 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-89 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-90 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-91 m/z = 662.22 (C₄₅H₂₂DN₃OS = 662.82) P-92 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-93 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-94 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-95 m/z = 762.25 (C₅₃H₂₆D₅N₃OS = 762.94) P-96 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-97 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-98 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-99 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-100 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-101 m/z = 667.25 (C₄₅H₁₇D₁₀N₃OS = 667.85) P-102 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-103 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-104 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-105 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-106 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-107 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-108 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-109 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-110 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-111 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-112 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-113 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-114 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-115 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-116 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-117 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-118 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-119 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-120 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-121 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-122 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-123 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-124 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-125 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-126 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-127 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-128 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-129 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-130 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-131 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-132 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-133 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-134 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-135 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-136 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-137 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-138 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-139 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-140 m/z = 762.25 (C₅₃H₂₆D₅N₃OS = 762.94) P-141 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-142 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-143 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-144 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-145 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-146 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-147 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-148 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-149 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-150 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-151 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-152 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-153 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-154 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) p-155 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-156 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-157 m/z = 681.19 (C₄₅H₂₇N₃OS = 681.81) P-158 m/z = 681.19 (C₄₅H₂₇N₃OS = 681.81) P-159 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-160 m/z = 781.22 (C₅₅H₃₁N₃OS = 781.93)

Synthesis Example 2

The compounds (final products 2) represented by Formula (12) according to the present invention can be prepared by reacting Sub 3-1 and Sub 3-2 as shown in the following Reaction Scheme 4, but are not limited thereto.

Synthesis Example of 4-1

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF, and (9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl)boronic acid (8.8 g, 20 mmol), Pd(PPh₃)₄ (0.03 eq.), K2CO3 (3 eq.) and water were added and refluxed with stirring. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO₄ and concentrated. The resulting organic material was separated by silicagel column chromatography and recrystallization to obtain 9.2 g (yield: 72%) of the product.

Synthesis Example of 4-21

10-bromo-7-(pyridin-2-yl)-7H-benzo[c]carbazole (7.5 g, 2 mmol), dibenzo[b,d]furan-2-ylboronic acid (4.2 g, 20 mmol) were carried out in the same manner as 4-1 to obtain 6.5 g of the product (yield: 71%)

Synthesis Example of 4-25

9-([1,1′-biphenyl]-4-yl)-3-bromo-9H-carbazole (8.0 g, 20 mmol), (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.7 g, 20 mmol) were carried out in the same manner as 4-1 to obtain 9.2 g of the product (yield: 75%)

Synthesis Example of 4-31

3′-bromo-9-phenyl-9H-2,9′-bicarbazole (9.7 g, 20 mmol), (9-phenyl-9H-carbazol-3-yl)boronic acid (5.7 g, 20 mmol) were carried out in the same manner as 4-1 to obtain 9.5 g of the product (yield: 73%)

Synthesis Example of 4-32

3-bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazole (8.2 g, 20 mmol), (12-([1,1′:4′,1″-terphenyl]-4-yl)-12H-benzo[4,5]thieno[2,3-a]carbazol-3-yl)boronic acid (10.9 g, 20 mmol) were carried out in the same manner as 4-1 to obtain 11.5 g of the product (yield: 69%)

Synthesis Example of 4-34

4-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol), (4-(dibenzo[b,d]thiophen-3-yl)phenyl)boronic acid (6.1 g, 20 mmol) were carried out in the same manner as 4-1 to obtain 6.7 g of the product (yield: 67%)

Synthesis Example of 4-35

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol), 9(9,9-dimethyl-9H-fluoren-3-yl)boronic acid (4.8 g, 20 mmol) were carried out in the same manner as 4-1 to obtain 6.1 g of the product (yield: 70%)

TABLE 4 compound FD-MS 4-1 m/z = 639.24 (C₄₅H₂₉N₅ = 639.75) 4-2 m/z = 715.27 (C₅₁H₃₃N₅ = 715.84) 4-3 m/z = 780.33 (C₅₇H₄₀N₄ = 780.95) 4-4 m/z = 639.24 (C₄₅H₂₉N₅ = 639.75) 4-5 m/z = 715.27 (C₅₁H₃₃N₅ = 715.84) 4-6 m/z = 780.33 (C₅₇H₄₀N₄ = 780.95) 4-7 m/z = 612.23 (C₄₄H₂₈N₄ = 612.72) 4-8 m/z = 612.23 (C₄₄H₂₈N₄ = 612.72) 4-9 m/z = 662.25 (C₄₈H₃₀N₄ = 662.78) 4-10 m/z = 484.19 (C₃₆H₂₄N₂ = 484.59) 4-11 m/z = 639.24 (C₄₅H₂₉N₅ = 639.75) 4-12 m/z = 715.27 (C₅₁H₃₃N₅ = 715.84) 4-13 m/z = 715.27 (C₅₁H₃₃N₅ = 715.84) 4-14 m/z = 638.25 (C₄₆H₃₀N₄ = 638.76) 4-15 m/z = 579.18 (C₄₀H₂₅N₃S = 579.71) 4-16 m/z = 410.14 (C₂₉H₁₈N₂S = 410.47) 4-17 m/z = 486.17 (C₃₅H₂₂N₂O = 486.56) 4-18 m/z = 486.17 (C₃₅H₂₂N₂O = 486.56) 4-19 m/z = 486.17 (C₃₅H₂₂N₂O = 486.56) 4-20 m/z = 563.20 (C₄₀H₂₅N₃O = 563.65) 4-21 m/z = 460.16 (C₃₃H₂₀N₂O = 460.52) 4-22 m/z = 536.19 (C₃₉H₂₄N₂O = 536.62) 4-23 m/z = 689.26 (C₄₉H₃₁N₅ = 689.80) 4-24 m/z = 585.22 (C₄₃H₂₇N₃ = 585.69) 4-25 m/z = 610.24 (C₄₆H₃₀N₂ = 610.76) 4-26 m/z = 610.24 (C₄₆H₃₀N₂ = 610.76) 4-27 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80) 4-28 m/z = 636.26 (C₄₈H₃₂N₂ = 636.80) 4-29 m/z = 610.24 (C₄₆H₃₀N₂ = 610.76) 4-30 m/z = 610.24 (C₄₆H₃₀N₂ = 610.76) 4-31 m/z = 649.25 (C₄₈H₃₁N₃ = 649.80) 4-32 m/z = 832.25 (C₆₀H₃₆N₂OS = 833.02) 4-33 m/z = 560.23 (C₄₂H₂₈N₂ = 560.70) 4-34 m/z = 501.16 (C₃₆H₂₃NS = 501.65) 4-35 m/z = 435.20 (C₃₃H₂₅N = 435.57) 4-36 m/z = 725.28 (C₅₄H₃₅N₃ = 725.90) 4-37 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-38 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-39 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-40 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-41 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-42 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-43 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-44 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-45 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-46 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-47 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-48 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-49 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-50 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-51 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-52 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84)

Synthesis Example 3

Final products represented by Formula (18) according to the present invention can be prepared by reacting as follows, but are not limited thereto. Synthesis Example of 13-17

9-(4′-bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene, and di([1,1′-biphenyl]-4-yl)amine (6.4 g, 20 mmol), Pd₂(dba)₃ (0.05 eq.), PPh₃ (0.1 eq.), NaOt-Bu (3 eq.) were added and refluxed with stirring at 100° C. at 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO₄ and concentrated. The resulting organic material was separated by silicagel column chromatography and recrystallization to obtain 12.9 g (yield: 84%) of the product.

Synthesis Example of 13-32

3-(4-bromophenyl)-9-phenyl-9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene, and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), Pd₂(dba)₃ (0.05 eq.), PPh₃ (0.1 eq.), NaOt-Bu (3 eq.) were added and refluxed with stirring at 100° C. at 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO₄ and concentrated. The resulting organic material was separated by silicagel column chromatography and recrystallization to obtain 13.8 g (yield: 85%) of the product.

Synthesis Example of 2-34

In a round bottom flask, Sub 4(19) (9.5 g, 20 mmol), Sub 5(4) (4.7 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene (300 mL) were added and were carried out at 100° C. When the reaction was complete, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 9.8 g (yield: 78%) of 2-34.

Synthesis Example of 2-58

In a round bottom flask, Sub 4(35) (8.4 g, 20 mmol), Sub 5(7) (5.7 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give 2-58 (10.4 g, 83%).

Synthesis Example of 2-59

In a round bottom flask, Sub 4(32) (12.9 g, 20 mmol), Sub 5(11) (7.9 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give 2-59 (5.2 g, 79%).

Synthesis Example of 2-69

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), 4-(2-bromophenyl)-9,9-diphenyl-9H-fluorene (9.5 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give 2-69 (12.2 g, 81%).

Synthesis Example of 2-71

In a round bottom flask, N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (7.5 g, 20 mmol), N-(3-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (10.6 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give 2-71 (12.9 g, 78%).

Synthesis Example 4

Final products represented by Formula (30) according to the present invention can be prepared by reacting Sub 30 and Sub 31 as shown in Reaction Scheme 5 below, but are not limited thereto.

Synthesis Example of Sub 30

Synthesis Example of Sub 30(81)

In a round bottom flask, 3-(9-phenyl-9H-fluoren-9-yl)aniline (6.7 g, 20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give Sub 30(81). (8.83 g, 84%).

Examples of Sub 31

Examples of Sub 31 are as follows, but are not limited thereto.

TABLE 5 compound FD-MS Sub 31-1 m/z = 155.96 (C₆H₅Br = 157.01) Sub 31-2 m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 31-3 m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 31-4 m/z = 231.99 (C₁₂H₉Br = 233.10) Sub 31-5 m/z = 309.02 (C₁₇H₁₂BrN = 310.19) Sub 31-6 m/z = 311.01 (C₁₅H₁₀BrN₃ = 312.16) Sub 31-7 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 31-8 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 31-9 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 31-10 m/z = 387.04 (C₂₁H₁₄BrN₃ = 388.26) Sub 31-11 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 31-12 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 31-13 m/z = 348.03 (C₁₉H₁₃BrN₂ = 349.22) Sub 31-14 m/z = 271.99 (C₁₃H₉BrN₂ = 273.13) Sub 31-15 m/z = 283.99 (C₁₄H₉BrN₂ = 285.14) Sub 31-16 m/z = 374.01 (C₂₀H₁₁BrN₂O = 375.22) Sub 31-17 m/z = 400.06 (C₂₃H₁₇BrN₂ = 401.30) Sub 31-18 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub 31-19 m/z = 476.09 (C₂₉H₂₁BrN₂ = 477.39)

Synthesis Example of 2-72

In a round bottom flask, N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)dibenzo[b,d]furan-1-amine (10.0 g, 20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give 2-72. (11.1 g, 80%).

Synthesis Example of 2-81

In a round bottom flask, Sub 30(81) (10.3 g, 20 mmol), Sub 31-4 (4.66 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out in the same manner as in 2-34 to give 2-81. (10.3 g, 76%).

TABLE 6 Compound FD-MS 2-81 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-82 m/z = 651.26 (C₄₉H₃₃NO = 651.81) 2-83 m/z = 641.22 (C₄₇H₃₁NS = 641.83) 2-84 m/z = 700.29 (C₅₃H₃₆N₂ = 700.89) 2-85 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-86 m/z = 651.26 (C₄₉H₃₃NO = 651.81) 2-87 m/z = 843.30 (C₆₃H₄₁NS = 844.09) 2-88 m/z = 701.28 (C₅₂H₃₅N₃ = 701.87) 2-89 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-90 m/z = 729.28 (C₅₃H₃₅N₃O = 729.88) 2-91 m/z = 912.29 (C₆₄H₄₀N₄OS = 913.11) 2-92 m/z = 878.34 (C₆₅H₄₂N₄ = 879.08) 2-93 m/z = 805.35 (C₆₀H₄₃N₃ = 806.03) 2-94 m/z = 906.34 (C₆₆H₄₂N₄O = 907.09) 2-95 m/z = 769.26 (C₅₅H₃₅N₃S = 769.97) 2-96 m/z = 884.30 (C₆₃H₄₀N₄S = 885.10) 2-97 m/z = 767.36 (C₅₉H₄₅N = 768.02) 2-98 m/z = 815.32 (C₆₂H₄₁NO = 816.02) 2-99 m/z = 829.28 (C₆₂H₃₉NS = 830.06) 2-100 m/z = 781.35 (C₅₉H₃₅D₅N₂ = 782.01) 2-101 m/z = 695.30 (C₅₂H₃₈FN = 695.88) 2-102 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-103 m/z = 803.36 (C₆₂H₄₅N = 804.05) 2-104 m/z = 6829.37 (C₆₄H₄₇N = 830.09) 2-105 m/z = 918.40 (C₇₀H₅₀N₂ = 919.18) 2-106 m/z = 601.28 (C₄₆H₃₅N = 601.79) 2-107 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-108 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-109 m/z = 701.31 (C₅₄H₃₉N = 701.91) 2-110 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-111 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-112 m/z = 682.34 (C₅₂H₃₄D₅N = 682.92) 2-113 m/z = 701.31 (C₅₄H₃₉N = 701.91) 2-114 m/z = 619.27 (C₄₆H₃₄FN = 619.78) 2-115 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-116 m/z = 803.36 (C₆₂H₄₅N = 804.05) 2-117 m/z = 701.31 (C₅₄H₃₉N = 701.91) 2-118 m/z = 651.29 (C₅₀H₃₇N = 651.85) 2-119 m/z = 727.32 (C₅₆H₄₁N = 727.95) 2-120 m/z = 758.37 (C₅₈H₃₈D₅N = 759.02) 2-121 m/z = 757.37 (C₅₈H₄₇N = 758.02) 2-122 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-123 m/z = 803.36 (C₆₂H₄₅N = 804.05) 2-124 m/z = 834.40 (C₆₄H₄₂D₅N = 835.12) 2-125 m/z = 883.33 (C₆₆H₄₅NS = 884.15) 2-126 m/z = 651.26 (C₄₉H₃₃NO = 651.81) 2-127 m/z = 641.22 (C₄₇H₃₁NS = 641.83) 2-128 m/z = 700.29 (C₅₃H₃₆N₂ = 700.89) 2-129 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-130 m/z = 651.26 (C₄₉H₃₃NO = 651.81) 2-131 m/z = 843.30 (C₆₃H₄₁NS = 844.09) 2-132 m/z = 701.28 (C₅₂H₃₅N₃ = 701.87) 2-133 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-134 m/z = 729.28 (C₅₃H₃₅N₃O = 729.88) 2-135 m/z = 912.29 (C₆₄H₄₀N₄OS = 913.11) 2-136 m/z = 878.34 (C₆₅H₄₂N₄ = 879.08) 2-137 m/z = 805.35 (C₆₀H₄₃N₃ = 806.03) 2-138 m/z = 906.34 (C₆₆H₄₂N₄O = 907.09) 2-139 m/z = 769.26 (C₅₅H₃₅N₃S = 769.97) 2-140 m/z = 884.30 (C₆₃H₄₀N₄S = 885.10) 2-141 m/z = 767.36 (C₅₉H₄₅N = 768.02) 2-142 m/z = 815.32 (C₆₂H₄₁NO = 816.02) 2-143 m/z = 829.28 (C₆₂H₃₉NS = 830.06) 2-144 m/z = 781.35 (C₅₉H₃₅D₅N₂ = 782.01) 2-145 m/z = 695.30 (C₅₂H₃₈FN = 695.88) 2-146 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-147 m/z = 803.36 (C₆₂H₄₅N = 804.05) 2-148 m/z = 6829.37 (C₆₄H₄₇N = 830.09) 2-149 m/z = 918.40 (C₇₀H₅₀N₂ = 919.18) 2-150 m/z = 717.34 (C₅₅H₄₃N = 717.96) 2-151 m/z = 717.34 (C₅₅H₄₃N = 717.96) 2-152 m/z = 717.34 (C₅₅H₄₃N = 717.96) 2-153 m/z = 717.34 (C₅₅H₄₃N = 717.96)

Evaluation of Manufacture of Organic Electronic Element Example 1) Manufacture and Evaluation of Green Organic Light Emitting Diode (Host)

First, on an ITO layer (anode) formed on a glass substrate, N-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenyl benzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and on the layer, 4,4-bis [N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as hole transport compounds to form a hole transport layer with a thickness of 60 nm. Subsequently, the inventive compound represented by Formula (1) was used as a host, and an emitting layer with a thickness of 30 nm was deposited as a dopant on the hole transport layer by doping Ir(ppy)₃[tris(2-phenylpyridine)-iridium] with a weight of 95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited as an electron transport layer to a thickness of 40 nm. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 1˜4

An OLED was prepared in the same manner as in Example 1, except that Comparative Compound A, Comparative Compound B, Comparative Compound C and Comparative Compound D were used as a host.

Comparative Compounds:

TABLE 7 Current Bright- Density ness Efficiency CIE compound Voltage (mA/cm²) (cd/m²) (cd/A) T(95) x y comparative comparative 5.9 24.9 5000.0 20.1 66.1 0.33 0.61 example(1) compound A comparative comparative 5.6 19.4 5000.0 25.8 71.3 0.32 0.63 example(2) compound B comparative comparative 5.7 23.1 5000.0 21.6 75.7 0.31 0.64 example(3) compound C comparative comparative 5.5 16.8 5000.0 29.7 80.1 0.30 0.61 example(4) compound D example(1) P-8 5.3 13.8 5000.0 36.1 91.5 0.34 0.62 example(2) P-29 5.0 13.5 5000.0 37.1 98.5 0.34 0.61 example(3) P-32 5.4 13.8 5000.0 36.3 87.6 0.30 0.64 example(4) P-61 5.1 12.7 5000.0 39.4 94.6 0.31 0.61 example(5) P-91 5.0 12.6 5000.0 39.6 93.3 0.33 0.63 example(6) P-146 5.1 12.5 5000.0 39.9 94.3 0.35 0.60 example(7) P-154 5.1 12.6 5000.0 39.6 94.2 0.33 0.64 example(8) P-156 5.2 13.6 5000.0 36.7 93.0 0.31 0.60

Example 2) Manufacture and Evaluation of Green Organic Light Emitting Diode (Mixed Host)

First, on an ITO layer (anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenyl benzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and on the layer, 4,4-bis [N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as hole transport compounds to form a hole transport layer with a thickness of 60 nm. Subsequently, a mixture of the inventive compound represented by Formula (1) and the compound represented by Formula (12) in a ratio of 6:4 was used as a host, and as a dopant, an emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping Ir(ppy)₃[tris(2-phenylpyridine)-iridium] with a weight of 95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited as an electron transport layer to a thickness of 40 nm. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 5˜8, 10˜13

An OLED was prepared in the same manner as in Example 2, except that Comparative Compound A, Comparative Compound B, Comparative Compound C, and Comparative Compound D were used as a host instead of the inventive compound represented by Formula (1).

Comparative Example 9 and 14

An OLED was prepared in the same manner as in Example 2, except for using the comparative compound E instead of the inventive compound represented by Formula (12) as a host,

TABLE 8 Bright- Second Current ness Lifetime First host host Voltage Density (cd/m²) Efficiency T(95) comparative comparative 4-27 5.3 21.4 5000.0 23.4 120.4 example(5) compound A comparative comparative 5.2 17.3 5000.0 28.9 124.8 example(6) compound B comparative comparative 5.1 19.9 5000.0 25.1 129.6 example(7) compound C comparative comparative 5.0 15.0 5000.0 33.3 133.2 example(8) compound D comparative comparative 5.0 12.9 5000.0 38.8 110.1 example(9) compound E comparative comparative 4-31 5.2 22.0 5000.0 22.7 109.8 example(10) compound A comparative comparative 5.0 17.7 5000.0 28.2 115.4 example(11) compound B comparative comparative 4.8 20.2 5000.0 24.8 119.1 example(12) compound C comparative comparative 4.7 16.2 5000.0 30.9 123.3 example(13) compound D comparative comparative 5.3 13.2 5000.0 37.9 101.7 example(14) compound E example(9) P-8 4-27 4.7 12.2 5000.0 41.0 133.7 example(10) P-29 4.4 11.1 5000.0 45.2 142.8 example(11) P-32 4.8 12.3 5000.0 40.6 130.1 example(12) P-61 4.5 11.8 5000.0 42.5 135.7 example(13) P-91 4.5 11.7 5000.0 42.8 135.3 example(14) P-146 4.5 11.9 5000.0 42.0 135.9 example(15) P-154 4.5 11.9 5000.0 42.1 135.3 example(16) P-156 4.7 12.2 5000.0 40.9 131.4 example(17) P-8 4-31 4.2 12.2 5000.0 40.9 130.9 example(18) P-29 4.1 11.1 5000.0 45.0 140.4 example(19) P-32 4.6 12.4 5000.0 40.4 128.2 example(20) P-61 4.3 11.8 5000.0 42.5 133.5 example(21) P-91 4.4 11.8 5000.0 42.4 130.1 example(22) P-146 4.2 11.8 5000.0 42.3 132.4 example(23) P-154 4.4 11.9 5000.0 42.2 133.9 example(24) P-156 4.6 12.3 5000.0 40.6 129.7

Example 3) Manufacture and Evaluation of Green Organic Light Emitting Diode (Emitting Auxiliary Layer+Mixed Host)

First, on an ITO layer (anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. Subsequently, on the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as an hole transport compound to a thickness of 60 nm to form a hole transport layer. Subsequently, the inventive compound represented by Formula (18) was vacuum-deposited as an emitting auxiliary layer material to a thickness of 20 nm to form an emitting auxiliary layer. After forming the emitting auxiliary layer, a mixture of the inventive compound represented by Formula (1) and the compound represented by Formula (12) in a ratio of 6:4 was used on the emitting auxiliary layer, and as a dopant, an emitting layer with a thickness of 30 nm was deposited by doping Ir(ppy)₃[tris(2-phenylpyridine)-iridium] with a weight of 95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited as an electron transport layer to a thickness of 40 nm. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 15˜29

An OLED was prepared in the same manner as in Example 3, except that the comparative compound A to E are each used instead of the inventive compound represented by Formula (1) as a host,

TABLE 9 Emitting Bright- Life- auxiliary Second Volt- Current ness time layer First host host age Density (cd/m²) Efficiency T(95) comparative 2-69 comparative 4-27 5.2 16.6 5000.0 30.1 125.1 example(15) compound A comparative comparative 5.2 13.8 5000.0 36.2 130.1 example(16) compound B comparative comparative 5.0 16.2 5000.0 30.8 135.3 example(17) compound C comparative comparative 5.0 12.6 5000.0 39.7 138.4 example(18) compound D comparative comparative 5.4 11.0 5000.0 45.4 115.6 example(19) compound E example(25) P-8 4.6 9.8 5000.0 51.1 140.4 example(26) P-29 4.3 9.0 5000.0 55.7 150.9 example(27) P-61 4.4 9.6 5000.0 52.2 144.5 example(28) P-146 4.4 9.7 5000.0 51.6 143.8 comparative 2-72 comparative 5.1 14.1 5000.0 35.4 130.4 example(20) compound A comparative comparative 5.0 12.1 5000.0 41.3 135.9 example(21) compound B comparative comparative 4.9 13.9 5000.0 35.9 140.7 example(22) compound C comparative comparative 5.0 11.4 5000.0 43.7 143.1 example(23) compound D comparative comparative 5.3 10.6 5000.0 47.1 120.3 example(24) compound E example(29) P-8 4.4 8.3 5000.0 59.9 145.9 example(30) P-29 4.0 7.7 5000.0 65.1 157.4 example(31) P-61 4.2 8.2 5000.0 60.7 150.1 example(32) P-146 4.3 8.2 5000.0 61.1 149.4 comparative 2-74 comparative 5.0 13.9 5000.0 36.1 130.8 example(25) compound A comparative comparative 5.1 12.0 5000.0 41.7 136.1 example(26) compound B comparative comparative 4.8 14.2 5000.0 35.3 141.2 example(27) compound C comparative comparative 4.9 11.5 5000.0 43.4 143.7 example(28) compound D comparative comparative 5.1 9.8 5000.0 50.8 120.9 example(29) compound E example(33) P-8 4.3 8.5 5000.0 59.1 146.2 example(34) P-29 3.9 7.7 5000.0 64.8 157.8 example(35) P-61 4.0 8.3 5000.0 60.3 150.6 example(36) P-146 4.1 8.2 5000.0 60.9 150.4 comparative 2-82 comparative 4.9 10.4 5000.0 48.2 141.8 example(30) compound A comparative comparative 4.9 10.2 5000.0 48.8 142.4 example(31) compound B comparative comparative 4.8 10.3 5000.0 48.5 143.7 example(32) compound C comparative comparative 4.9 10.0 5000.0 50.1 145.3 example(33) compound D comparative comparative 4.9 9.9 5000.0 50.5 140.9 example(34) compound E example(37) P-8 3.7 8.0 5000.0 62.5 160.8 example(38) P-29 3.7 7.6 5000.0 65.4 163.8 example(39) P-61 3.6 7.7 5000.0 64.8 163.2 example(40) P-146 3.6 8.0 5000.0 62.8 161.5

Example 4) Manufacture and Evaluation of Green Organic Light Emitting Diode (Hole Transport Layer+Emitting Auxiliary Layer+Mixed Host)

First, on an ITO layer (anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. Subsequently, on the layer, the compound represented by Formula (18) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, the compound represented by Formula (18) was vacuum-deposited as an emitting auxiliary material to a thickness of 20 nm to form an emitting auxiliary layer. After forming the emitting auxiliary layer, a mixture of the inventive compound represented by Formula (1) and the compound represented by Formula (12) in a ratio of 6:4 was used as a host, and as a dopant, an emitting layer with a thickness of 30 nm was deposited by doping Ir(ppy)₃[tris(2-phenylpyridine)-iridium] with a weight of 95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

TABLE 10 Hole trans- Emitting Bright- Life- port auxiliary First Second Current ness time layer layer host host Voltage Density (cd/m²) Efficiency T(95) example(37) 13-32 2-72 P-8 4-27 4.2 7.8 5000.0 64.2 149.1 example(38) P-29 3.9 7.1 5000.0 70.1 160.6 example(39) P-61 4.1 7.6 5000.0 65.9 155.8 example(40) P-146 4.2 7.6 5000.0 66.2 154.3 example(41) 2-74 P-8 4.0 7.8 5000.0 63.8 151.4 example(42) P-29 3.8 7.2 5000.0 69.7 162.1 example(43) P-61 3.9 7.6 5000.0 65.4 155.8 example(44) P-146 3.8 7.6 5000.0 66.0 155.7 example(45) 2-72 P-8 4.2 7.8 5000.0 64.2 149.1 example(46) P-29 3.9 7.1 5000.0 70.1 160.6 example(47) P-61 4.1 7.6 5000.0 65.9 155.8 example(48) P-146 4.2 7.6 5000.0 66.2 154.3 example(49) 2-74 P-8 4.0 7.8 5000.0 63.8 151.4 example(50) P-29 3.8 7.2 5000.0 69.7 162.1 example(51) P-61 3.9 7.6 5000.0 65.4 155.8 example(52) P-146 3.8 7.6 5000.0 66.0 155.7 example(53) 2-82 P-8 3.4 7.3 5000.0 68.9 163.6 example(54) P-29 3.2 6.8 5000.0 73.4 168.7 example(55) P-61 3.3 7.1 5000.0 70.2 166.7 example(56) P-146 3.3 7.2 5000.0 69.3 165.4

As can be seen from the results of Table 7 to 10, the organic electronic element using the organic electronic device material of the present invention as a phosphorescent host can remarkably improve the high luminous efficiency, the low driving voltage and the lifetime.

Table 7 shows the superiority of the compounds of the invention compared to the comparative compounds when the inventive compound represented by Formula (1) was used as a single host. In the results of Comparative Compound A and Comparative Compound C, when the 3-dibenzofuran was substituted, the performance was improved in all aspects of driving voltage, efficiency and lifetime, compared with 4-dibenzofuran. In the results of Comparative Compound A and Comparative Compound B, or Comparative Compound C and Comparative Compound D, it can be confirmed that the performance of the triazine substituted with two dibenzothiophen or dibenzofuran moiety is improved compared with the triazine substituted with one dibenzothiophen or dibenzofuran moiety. Thus, it can be finally confirmed that the inventive compound, in which triazine is substituted with 3-dibenzofuran and is linked by a linker with 4-dibenzothiophen to the other side, exhibits an improved result which is significantly different from the comparative compounds A to D. It is suggested that the energy level (HOMO, LUMO, T1, etc.) of the compound may vary significantly depending on the kind of the substituent or the substitution position, and the differences in the physical properties of compounds may act as key factors (ex. energy balance) in improving device performance during device deposition, resulting in different device results.

Table 8 shows that when the compound represented by Formula (12) and the compound of Formula (1) are mixed, they are significantly better than other comparison combinations. This result is also supported the explanations in the case of a single host, and when bonded to Formula (12), the driving and efficiency can be improved by about 24% and the lifetime can be improved by about 63% compared with a single host. When two hosts are premixed, the aging rate is very important to deposit at a certain rate, and the compound of the present invention was superior in the aging rate compared with other materials, and particularly, the compound that at least one of Ar¹, Ar³ and R³ is a C₆-C₂₄ aryl group has the best results in the aging test.

Table 9 is the examples using the mixed compound of Formula (1) and Formula (12) as the emitting layer host and using the compound represented by Formula (18) in the emitting auxiliary layer, and shows that the efficiency is improved by about 60% and the lifetime is improved by about 20% compared with Table 8. Here, using the compound represented by Formula (18) as the hole transport compound also yielded slightly improved results in terms of driving voltage, efficiency, and lifetime in comparison with the results in Table 7.

That is, the compound of the present invention exhibits improved results compared with the known compounds even when used as a single host, but when used in combination with the compound represented by Formula (12), or when the compound represented by Formula (18) was used for the emitting auxiliary layer or the hole transport layer, remarkable results were obtained.

Example 5) Manufacture and Evaluation of Blue Organic Light Emitting Diode

First, on an ITO layer (anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. Subsequently, and on the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, the inventive compound was vacuum-deposited as an emitting auxiliary layer material to a thickness of 20 nm to form an emitting auxiliary layer. After forming the emitting auxiliary layer, on the emitting auxiliary layer, 9,10-di(naphthalen-2-yl)anthracene is used as a host, and BD-052X (Idemitsu kosan) is used as dopant in a ratio of 96:4, therefore an emitting layer with a thickness of 30 nm was deposited on the emitting auxiliary layer. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 35˜37

An OLED was prepared in the same manner as in Comparative Example 5 except that the emitting auxiliary layer was not used and Comparative Compound F, Comparative Compound G and Invention Compound 2-81 were used as the hole transport layer material.

Comparative Example 38

An OLED was prepared in the same manner as in Comparative Example 5 except that the emitting auxiliary layer was not used.

Comparative Examples 39˜40

An OLED was prepared in the same manner as in Comparative Example 5 except that the Comparative Compound F or Comparative Compound G were used as the emitting auxiliary layer material.

TABLE 11 Emitting Hole auxiliary Current bright- transport layer volt- density ness Efficiency compound compound age (mA/cm²) (cd/m²) (cd/A) T(95) comparative comparative — 6.8 14.3 500.0 3.5 70.4 example (35) compound F comparative comparative 7.0 15.2 500.0 3.3 69.6 example (36) compound G comparative 2-81 6.9 13.5 500.0 3.7 71.2 example (37) comparative NPB — 7.3 17.9 500.0 2.8 65.3 example (38) comparative comparative 6 .8 11.1 500.0 4.5 80.4 example (39) compound F comparative comparative 6 .5 10.2 500.0 4.9 81.7 example (40) compound G example(57) 2-81 6.3 9.1 500.0 5.5 94.9 example(58) 2-83 6.2 8.6 500.0 5.8 97.0 example(59) 2-85 6.1 9.2 500.0 5.4 93.2 example(60) 2-86 6.2 8.9 500.0 5.6 96.9 example(61) 2-89 6.1 9.3 500.0 5.4 94.1 example(62) 2-107 6.1 9.3 500.0 5.4 94.8 example(63) 2-122 6.0 9.1 500.0 5.5 94.7 example(64) 2-127 6.2 8.8 500.0 5.7 96.0 example(65) 2-128 6.1 8.7 500.0 5.7 95.6 example(66) 2-133 6.1 9.4 500.0 5.3 94.3 example(67) 2-150 6.2 9.2 500.0 5.4 93.6 example(68) 2-151 6.0 9.4 500.0 5.3 94.1 example(69) 2-152 6.0 9.1 500.0 5.5 93.7 example(70) 2-153 6.1 9.4 500.0 5.3 93.2

Example 6) Manufacture and Evaluation of Green Organic Light Emitting Diode

First, on an ITO layer (anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. Subsequently, and on the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviated as NPD) was vacuum-deposited as a hole transport compound to a thickness of 60 nm to form a hole transport layer. Subsequently, the inventive compound represented by Formula (30) was vacuum-deposited as an emitting auxiliary layer material to a thickness of 20 nm to form an emitting auxiliary layer. After forming the emitting auxiliary layer, on the emitting auxiliary layer, 4,4′-di(9H-carbazol-9-yl)-1,1′-biphenyl is used as a host, and Ir(ppy)₃[tris(2-phenylpyridine)-iridium] is used as dopant in a ratio of 95:5, and an emitting layer with a thickness of 30 nm was deposited. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 41˜42

An OLED was prepared in the same manner as in Comparative Example 5 except that Comparative Compound F or Comparative Compound G were used as the emitting auxiliary layer material.

TABLE 12 Current bright- density ness Efficiency CIE compound voltage (mA/cm²) (cd/m²) (cd/A) T(95) x y comparative comparative 7.3 17.4 5000.0 28.7 80.4 0.30 0.61 example(41) compound F comparative comparative 7.4 19.9 5000.0 25.1 80.9 0.33 0.64 example(42) compound G example(71) 2-81 5.6 11.0 5000.0 45.4 120.3 0.31 0.64 example(72) 2-83 6.3 14.2 5000.0 35.1 104.3 0.31 0.64 example(73) 2-85 5.8 13.8 5000.0 36.2 110.1 0.34 0.61 example(74) 2-86 6.4 14.3 5000.0 35.0 103.6 0.33 0.63 example(75) 2-89 6.0 14.1 5000.0 35.5 113.0 0.33 0.65 example(76) 2-107 5.8 11.3 5000.0 44.3 112.6 0.32 0.65 example(77) 2-122 5.9 11.4 5000.0 43.8 112.3 0.34 0.63 example(78) 2-127 6.4 12.6 5000.0 39.8 104.2 0.33 0.65 example(79) 2-128 6.3 12.8 5000.0 39.2 102.5 0.32 0.65 example(80) 2-133 5.9 12.5 5000.0 39.9 111.2 0.32 0.65 example(81) 2-150 5.4 11.4 5000.0 43.8 114.8 0.31 0.64 example(82) 2-151 5.2 11.2 5000.0 44.8 111.5 0.30 0.63 example(83) 2-152 5.2 11.6 5000.0 43.1 112.1 0.31 0.63 example(84) 2-153 5.3 11.2 5000.0 44.8 114.4 0.30 0.62

As can be seen from the results of Table 11 to 12, when OLED was manufactured by using the material for an organic electroluminescence device of the present invention as an emitting auxiliary layer material, the driving voltage of the organic electroluminescent device can be lowered and the luminous efficiency and lifetime can be remarkably improved as compared with the comparative example not using the material for the emitting auxiliary layer or using the comparative compound F or the comparative compound G.

Table 11 shows the results of the production of a blue organic light emitting device. It can be confirmed that excellent results are obtained when the compound of the present invention is used as an emitting auxiliary layer. The results of Comparative Example 39 or Comparative Example 40 and Examples 57 to 70 show that compounds of the present invention substituted with specific substituents such as DBT, DBF, Cz, and Fluorene are remarkably superior to the comparative compounds substituted with the general aryl group even though the mother compound is similar. That is, when specific substituents such as DBT, DBF, Cz, and Fluorene are introduced, the refractive index, the Tg, and the energy level of the compound (HOMO, LUMO, T1, etc.) become significantly different, and this difference in physical properties is a major factor in improving the device performance during device deposition (for example, such as an energy balance), such that different device results can be derived.

Table 12 shows the results of the production of a green organic light emitting device. When the compound of the present invention was used as an emitting auxiliary layer, the results were significantly superior to the comparative compounds. This is also the effect of certain substituents such as DBT, DBF, Cz, and Fluorene, and a specific feature is that the superiority of the green auxiliary layer is significantly improved than the blue auxiliary layer. Further, in the case of the blue auxiliary layer, DBT and DBF substituted compounds showed the most excellent properties, but the results of the green auxiliary layer showed the best results with the Fluorene substituted compounds. This suggests that even if the emitting auxiliary layer compound is the same, the properties required depending on the color of the emitting layer are different, so that a result which can not be deduced by those skilled in the art can be obtained.

Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Therefore, the embodiment disclosed in the present invention is intended to illustrate the scope of the technical idea of the present invention, and the scope of the present invention is not limited by the embodiment. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention. 

1. A compound represented by Formula (1):

wherein: 1) Ar¹, Ar² and Ar³ are each independently a C₆-C₆₀ aryl group, 2) l+e is an integer of 0 to 4, d+m is an integer of 0 to 4, a and b are an integer of 0 to 3, n is an integer of 1 to 3, c is an integer of 0 to 4, 3) R¹, R², R³, R⁴ and R⁵ are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)), wherein L′ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; and R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or a plurality of R¹, a plurality of R², a plurality of R³, a plurality of R⁴, and a plurality of R⁵ may be bonded to each other to form an aromatic ring or heteroaromatic ring, wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may be bonded to each other to form a ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed by the combination thereof and comprises a saturated or unsaturated ring.
 2. The compound according to claim 1, wherein the compound represented by Formula (1) is any one of the following Formulas (2) to (7):

wherein Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined in claim
 1. 3. The compound according to claim 1, wherein at least one of Ar¹, Ar², and R³ in Formula (1) is a C₆˜C₂₄ aryl group.
 4. The compound according to claim 1, wherein Ar¹ or Ar³ in Formula (1) is a C₆˜C₂₄ aryl group.
 5. The compound according to claim 1, wherein R³ in Formula (1) is a C₆˜C₂₄ aryl group.
 6. The compound according to claim 1, wherein Formula (1) is any one of the following Formulas (8) to (10):

wherein Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, n, R¹, R², R³, R⁴ and R⁵ are the same as defined in claim
 1. 7. The compound according to claim 1, wherein the compound represented by Formula (1) is Formula (11):

wherein Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined in claim
 1. 8. The compound according to claim 1, wherein the compound represented by Formula (1) is any one of the following compounds:


9. An organic electronic element comprising a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode and comprising a compound of Formula (1) according to claim
 1. 10. The organic electronic element according to claim 9, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emitting auxiliary layer, an emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and at least one of the hole injection layer, the hole transport layer, the emitting auxiliary layer, the emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer comprises one or more of the compounds of Formula (1).
 11. The organic electronic element according to claim 10, wherein the compound is included in the emitting layer.
 12. The organic electronic element according to claim 11, further comprising a compound represented by Formula (12) in the emitting layer:

wherein: 1) Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵ and Z¹⁶ are each independently CR or N, wherein R is hydrogen; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀ arylamine group; a fluorenyl group; and may form a ring by combining with neighboring groups, 2) L² is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a C₃-C₆₀ heteroarylene group; and a divalent aliphatic hydrocarbon group, 3) W is NAr⁵, O, S or CR′R″, wherein R′ and R″ are each independently selected from the group of a C₁-C₅₀ alkyl group; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bonded to each other to form a spiro ring, and 4) Ar⁴ and Ar⁵ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀ arylamine group; a fluorene group.
 13. The organic electronic element according to claim 12, wherein Formula (12) is any one of the following Formulas (13) to (16):

wherein Ar⁴, Ar⁵, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵, Z¹⁶, L², R′, R″ are the same as defined in claim
 12. 14. The organic electronic element according to claim 12, wherein both Ar⁴ and Ar⁵ in Formula (12) are a C₆-C₃₀ aryl group.
 15. The organic electronic element according to claim 12, wherein the compound represented by Formula (12) is a compound represented by Formula (17):

wherein: Ar⁴, Ar⁵, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵, Z¹⁶, and L² are the same as defined in claim 12, 1) L¹ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a C₃-C₆₀ heteroarylene group; and a divalent aliphatic hydrocarbon group, 2) Y is O, S or NAr⁵, 3) R^(a) and R^(b) are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or a plurality of R^(a) or a plurality of R^(b) may be bonded to each other to form an aromatic ring or and heteroaromatic ring, wherein, L′ may be selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; and the R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or a plurality of R¹, a plurality of R², a plurality of R³, a plurality of R⁴, and a plurality of R⁵ may be bonded to each other to form an aromatic ring or and heteroaromatic ring, and 4) y is an integer of 0 to 3, z is an integer of 0 to
 4. 16. The organic electronic element according to claim 12, wherein the compound represented by Formula (12) is any one of the following compounds:


17. An organic electronic element comprising an anode; a cathode; an organic material layer formed between the anode and the cathode, wherein the organic material layer includes an emitting layer, an hole transport layer formed between the anode and the emitting layer; an emitting auxiliary layer formed between the emitting layer and the hole transport layer; wherein the hole transport layer or the emitting auxiliary layer comprises a compound represented by Formula (18), wherein the emitting layer comprises a compound represented by Formula (1):

wherein: 1) Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are the same as defined in claim 1, 2) Ar⁴ and Ar⁵ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)), wherein, L′ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; and R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or Ar⁴ and Ar⁵ may be bonded to each other to form a ring, 3) Ar⁶ is selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; or is at least one of the following Formulas (1-a), (1-b), (1-c):

4) Ar⁹, Ar¹⁰ and Ar¹¹ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)), 5) h, i, and g are an integer of 0 to 4; j is an integer of 0 to 3; and R⁶, R⁷, R⁸ and R⁹ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)), wherein in case g, h, i, j are 2 or more, R⁶, R⁷, R⁸ and R⁹ are each in plural being the same or different and may be bonded to each other to form a ring, 6) L⁶ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P, and 7) L⁵ is selected from the group consisting of a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P.
 18. The organic electronic element according to claim 17, further comprising at least one of the compounds represented by Formula (12) in the emitting layer:

wherein: 1) Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵ and Z¹⁶ are each independently CR or N, wherein R is hydrogen; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀ arylamine group; a fluorene group; and is possible to form a ring by combining with neighboring groups, 2) L² is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a C₃-C₆₀ heteroarylene group; and a divalent aliphatic hydrocarbon group, 3) W is NAr⁵, O, S or CR′R″, wherein R′ and R″ are each independently a C₁-C₅₀ alkyl group; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bonded to each other to form a spiro ring, and 4) Ar⁴ and Ar⁵ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀ arylamine group; a fluorene group.
 19. The organic electronic element according to claim 17, wherein the hole transport layer comprises a compound represented by Formula (19) or Formula (20), and the emitting auxiliary layer comprises a compound represented by Formula (21) or Formula (22):

wherein: 1) Ar⁶ is selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P, and 2) Ar⁴, Ar⁵, Ar⁹, Ar¹⁰, Ar¹¹, h, i, g, L⁵, L⁶, R⁶, R⁷, R⁸ and R⁹ are the same as defined in claim
 17. 20. The organic electronic element according to claim 17, wherein the compound represented by Formula (18) is one of the following compounds:


21. The organic electronic element according to claim 17, wherein the compounds represented by Formula (1) and (18) are mixed in a ratio of 1:9 to 9:1 and used in the emitting layer.
 22. The organic electronic element according to claim 17, wherein the compound represented by Formula (1) is included in the emitting layer as a phosphorescent host material.
 23. The organic electronic element according to claim 17, further comprising a light efficiency enhancing layer formed on at least one of the opposite sides to the organic material layer among one side of the first electrode and of the second electrode.
 24. The organic electronic element according to claim 17, wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. 25.-34. (canceled)
 35. A display device comprising the organic electronic element of claim 9; and a control part driving the display device.
 36. A display device according to claim 35, wherein the organic electronic element is an OLED, an organic solar cell, an organic photo conductor (OPC), organic transistor (organic TFT), or an element for monochromic or white illumination.
 37. A display device comprising the organic electronic element of claim 17; and a control part driving the display device.
 38. A display device according to claim 37, wherein the organic electronic element is an OLED, an organic solar cell, an organic photo conductor (OPC), organic transistor (organic TFT), or an element for monochromic or white illumination. 